35405-94-8

Basic information

• Product Name: ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate
• Synonyms: ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate
• CAS NO: 35405-94-8
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.18
• Mol File: 35405-94-8.mol

Chemical Properties

• Boiling Point: 298.307 °C at 760 mmHg
• Flash Point: 134.212 °C
• Appearance: /
• Density: 1.288 g/cm³
• CAS DataBase Reference: ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate(35405-94-8)
• EPA Substance Registry System: ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate(35405-94-8)

Safety Data

• Hazardous Substances Data: 35405-94-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 56, p. 1429, 1978 DOI: 10.1139/v78-234

Upstream product

• 35355-49-8 ethyl 2-azido-3-(furan-2-yl)acrylate 
• 98-01-1 furfural 
• 71754-74-0 ethyl 2-azidopropanoate 
• 1501968-64-4 ethyl 4-benzoyl-4H-furo[3,2-b]pyrrole-5-carboxylate 
• 14757-78-9 3-bromofurfural 
• 1501968-56-4 C₁₆H₁₆BrNO₆ 

Downstream Products

• 67268-37-5 4H-furo[3,2-b]pyrrole-5-carboxylic acid 
• 80564-00-7 (3R,7bS)-3-Benzoyl-2-phenyl-3,3a,7,7b-tetrahydro-2H-pyrrolo[2',3':4,5]furo[2,3-d]isoxazole-6-carboxylic acid ethyl ester 
• 132120-25-3 ethyl 4-benzylfuro<3,2-b>pyrrole-5-carboxylate 
• 144658-77-5 4-(2-Nitro-benzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester 
• 144658-76-4 4-(4-Nitro-benzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid ethyl ester 
• 119118-10-4 4-benzylfuro<3,2-b>pyrrole 
• 144658-72-0 4-benzylfuro<3,2-b>pyrrole-5-carboxylic acid 
• 80709-74-6 4-Ethylfuro<3,2-b>pyrrole-5-carboxylic acid 
• 80564-03-0 C₂₃H₁₈N₂O₅ 
• 250-91-9 furo<3,2-b>pyrrole 
• 117613-30-6 4-methylfuro[3,2-b]pyrrole-5-carboxylic acid 
• 1309794-53-3 ethyl 4-(benzoyloxymethyl)-4H-furo[3,2-b]pyrrole-5-carboxylate 

Relevant articles and documents

The effect of single atom replacement on organic thin film transistors: Case of thieno[3,2-b] pyrrole vs. furo[3,2-b] pyrrole

Despite polypyrrole having higher conductivities compared to polythiophenes, pyrrole based materials have garnered less attention in the organic electronics community due to their instability in air. Construction of stable pyrrolic units could be achieved by fusing relatively unstable pyrrole with stable aromatic rings. In this report, we discuss and compare the organic field-effect transistor performances of the smallest S,N-heteroacene and O,N-heteroacene, thieno[3,2-b]pyrrole and furo[3,2-b]pyrrole, respectively, in donor-acceptor-donor type organic semiconducting small molecules. Since both building blocks are highly electron-rich, thiophene flanked 5,6-difluorobenzo[c][1,2,5]thiadiazole is employed as a central electron-withdrawing unit. The small molecule containing thieno[3,2-b]pyrrole exhibit moderate hole mobilities (10-3 cm2 V-1 s-1) irrespective of the annealing temperature. In contrast, the small molecule bearing furo[3,2-b]pyrrole is completely inactive in field-effect transistors. To the best of our knowledge this is the first report to compare the smallest units of S,N and O,N-heteroacenes for organic field-effect transistors.

PIKFYVE KINASE INHIBITORS

The present invention relates to compounds useful as inhibitors of phosphatidylinositol-3-phosphate 5-kinase (PIKfyve) as well as their use for treating diseases and disorders associated with PIKfyve.

TREATMENT OF VIRAL INFECTIONS WITH COMBINATION OF PIKFYVE KINASE INHIBITORS AND TMPRSS-2 INHIBITORS

The present invention relates to methods of treating viral infections including COVID-19 and compositions with a combination of (i) an inhibitor of phosphatidylinositol-3-phosphate 5-kinase (PIKfyve) and (ii) an inhibitor of transmembrane serine proteinase 2 (TMPRSS-2).

D-AMINO ACID OXIDASE INHIBITORS AND THERAPEUTIC USES THEREOF

The present invention relates to compounds of Formula (I): or a pharmaceutically acceptable salt thereof, wherein: each of A, B, C, D, and E, independently, is C, N, N—H, O, S, or absent is a single bond or a double bond; each of X, Y, and Z, independentl

PIKFYVE KINASE INHIBITORS

The present invention relates to compounds of formula (I) (shown below) useful as inhibitors of phosphatidylinositol- 3 -phosphate 5-kinase (PIKfyve) as well as their use for treating diseases and disorders associated with PIKfyve.

Thieno[3,2-b]pyrrole-5-carboxamides as New Reversible Inhibitors of Histone Lysine Demethylase KDM1A/LSD1. Part 1: High-Throughput Screening and Preliminary Exploration

Lysine specific demethylase 1 KDM1A (LSD1) regulates histone methylation and it is increasingly recognized as a potential therapeutic target in oncology. We report on a high-throughput screening campaign performed on KDM1A/CoREST, using a time-resolved fluorescence resonance energy transfer (TR-FRET) technology, to identify reversible inhibitors. The screening led to 115 hits for which we determined biochemical IC50, thus identifying four chemical series. After data analysis, we have prioritized the chemical series of N-phenyl-4H-thieno[3, 2-b]pyrrole-5-carboxamide for which we obtained X-ray structures of the most potent hit (compound 19, IC50 = 2.9 μM) in complex with the enzyme. Initial expansion of this chemical class, both modifying core structure and decorating benzamide moiety, was directed toward the definition of the moieties responsible for the interaction with the enzyme. Preliminary optimization led to compound 90, which inhibited the enzyme with a submicromolar IC50 (0.162 μM), capable of inhibiting the target in cells.

Structural Optimizations of Thieno[3,2-b]pyrrole Derivatives for the Development of Metabolically Stable Inhibitors of Chikungunya Virus

Chikungunya virus (CHIKV) is a re-emerging vector-borne alphavirus, and there is no approved effective antiviral treatment currently available for CHIKV. We previously reported the discovery of thieno[3,2-b]pyrrole 1b that displayed good antiviral activit

Practical nonazide synthesis of a D-amino acid oxidase inhibitor via a sequential erlenmeyer-ploechl reaction and ligand-free copper(I) amination protocol

A synthetic route to fused heterocycle 5 (R1 = Et) was developed that avoids the use of troublesome azido functionality. In this approach, 3-bromofuran aldehyde 7 was synthesized from 3-bromofuran 6 using highly regioselective formylation conditions. The crude solution of 7 was treated with hippuric acid under Erlenmeyer-Ploechl conditions to give enamide product 16, which was isolated by crystallization. Intramolecular amination/cyclization to the fused pyrrole was achieved under ligand-free Cu(I) catalysis in toluene, followed by diamine workup to remove the benzoyl protecting group and residual copper. The final product 5 (R1 = Et) was crystallized directly from the reaction mixture, providing up to 60% overall yield over five chemical steps and two isolations.

Indoles via Knoevenagel-Hemetsberger reaction sequence

A series of substituted indoles have been synthesized by the sequential reaction of aromatic aldehydes with ethyl azidoacetate in the presence of sodium ethoxide to form the corresponding ethyl α-azido-β-arylacrylates (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the ethyl α-azido-β-arylacrylates were significantly increased when employing the sacrificial electrophile ethyl trifluoroacetate. 1H NMR and coupled 1H-13C NMR analysis of the ethyl α-azido-β-arylacrylates indicate that the condensation is stereospecific - only the Z-isomer could be detected. Solvent mediated thermal treatment of the meta-substituted ethyl α-azido-β- arylacrylates resulted in the formation of both the 5- and 7- substituted indoles - the 5-regioisomer being slightly favored over the 7-regioisomer. Analogous thermal treatment of (2Z, 2Z′)-diethyl 3,3′-(1,3- phenylene)bis(2-azidoacrylate) and (2Z, 2Z′)-diethyl 3,3′-(1,4- phenylene)bis(2-azidoacrylate) exclusively produced pyrroloindoles, diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate and diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate, respectively. Results are also reported which indicate that the α-azido-β-arylacrylates can be used in the subsequent Hemetsberger indolization process without prior purification.

The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors

The 'NMDA hypofunction hypothesis of schizophrenia' can be tested in a number of ways. DAO is the enzyme primarily responsible for the metabolism of d-serine, a co-agonist for the NMDA receptor. We identified novel DAO inhibitors, in particular, acid 1, which demonstrated moderate potency for DAO in vitro and ex vivo, and raised plasma d-serine levels after dosing ip to rats. In parallel, analogues were prepared to survey the SARs of 1.